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Selected in the third round of the 2009 NFL draft out of Nichols State, Webb made a splash almost immediately. Webb won the team’s starting kick returner and in Week 8 returned a kick 95 yards for a touchdown. Injuries in 2011 forced Webb into the starting lineup where he excelled, notching five interceptions for 81 yards, including one returned for a touchdown.

Webb made the transition to safety from cornerback full time in 2016. However, it was multiple restructures that painted the Ravens into a corner regarding his contract. After the signing of safety Tony Jefferson, it was just a matter of when Webb would be released and Baltimore would get the $5.5 million in salary cap relief.